Cottage vacation rentals in Castleton

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Top-rated cottage rentals in Castleton

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Top guest favorite

A spacious backyard is featured, with green grass and several trees providing shade. Two green Adirondack chairs are positioned near a fire pit, surrounded by lush foliage. Sunlight casts long shadows across the lawn, enhancing the serene outdoor atmosphere.

Cottage in New Haven

4.99 out of 5 average rating, 270 reviews

Small New Haven Cozy Cottage

This very small, compact cottage is in a rural setting, off the beaten path. It is about a 12 minute drive to Middlebury where you can find shops, restaurants and Middlebury College. Burlington is about 40 minutes north of where we are located. Hiking/skiing in the Green Mountains, fly fishing in the nearby New Haven River, boating/swimming on Lake Champlain, and enjoying the many local craft breweries and wineries are some of the many activities you have access to from this beautiful spot.

Top guest favorite

Cottage in Leicester

4.97 out of 5 average rating, 274 reviews

Banjo's Cottage near Middlebury & Recreation Areas

Private getaway on our 200 acre organic farm with sunroom, wood stove, fully equipped kitchen & wifi. Level 2 EV charger. Walk to Fern Lake, hike/ski/bike our woods trails, explore Moosalamoo Recreation Area by foot, bike or kayak. Canoe Lake Dunmore, swim Silver Lake. 15 minutes to the Rikert Nordic Center, Blueberry Hill, and Middlebury Snow Bowl; an hour to Killington, Sugarbush & Mad River ski areas. Easy access to Middlebury College, golf courses, local breweries & top tier restaurants.

Top guest favorite

A serene river flows through a rocky landscape, surrounded by lush greenery. Sunlight reflects off the water, creating a calming ambiance. Two individuals can be seen wading in the shallow part of the river, enhancing the sense of a natural retreat.

Cottage in Poultney

4.97 out of 5 average rating, 135 reviews

The Cottage in East Poultney

The Cottage is located in historic East Poultney next to the old Poultney schoolhouse (now historical society). Just over 1 mile to the town of Poultney. The sidewalk starts (or ends how you look at it) in front of the cottage which leads to town. Great for a walk or bike ride. Pico, Killington and Bromley Mountains all less than an hour drive. Plentiful fishing and boating opportunities. 3 miles to Lake St Catherine, under 10 miles to Lake Bomoseen. Slate Valley bike trails surround the area.

Guest favorite

A rustic picnic table is set under leafy trees, surrounded by ferns and overlooking a serene river. A colorful tablecloth covers the table, which is adorned with dishes and decorative items, inviting guests to enjoy a meal in nature.

Cottage in Pawlet

4.96 out of 5 average rating, 130 reviews

Carriage Barn at Indian Hill

Our guest cottage is a lovely converted 1840s-era carriage barn nestled in the heart of the Mettawee Valley in the southwest corner of Vermont. It is decorated with antiques, artworks and an upright piano. Our 65 acres on scenic Indian Hill are available for hiking & snow-shoeing. We have 12 acres frontage on the Mettawee River, rated one of the best for fly fishing in VT. Ready access to many area attractions, from local swimming holes to skiing at nearby Bromley and Stratton mountains.

Guest favorite

Cottage in Lincoln

4.87 out of 5 average rating, 914 reviews

The Barn at North Orchard, Near Middlebury

Our barn sits on an 80 acre estate with fab views of the Green Mts. near Middlebury/Burlington. Perfect for 2 adults and a child or grandparents/ 2 friendly couples. Close to skiing, hiking, lake & river swimming, great restaurants... local beer, wine, cheese!. Want yoga, pasta class, or massage? We will gladly hook you up. Or, you could stay in to read, work, and enjoy the serenity of the mountains. A very private garden patio for morning coffee/ afternoon beer or wine or awaits you.

Top guest favorite

A wooden gate stands at the forefront, leading to a grassy area illuminated by soft solar lights along the path. In the background, a red barn and a building with warm lights hint at welcoming spaces under a cloudy evening sky.

Cottage in New Haven

4.99 out of 5 average rating, 175 reviews

Hilltop Cottage With a View

Our newly built cozy and relaxing guest cottage is located in New Haven . It has stunning views and gorgeous sunsets!! Located just seven miles from Middlebury ,Vergennes and Bristol . All of which have great shops and restaurants! Close to many local attractions including ,Woodchuck Cider house, Lincoln Peak Vineyard, Ski areas, Hiking , rivers, lakes, restaurants and much more! Our goal was to provide guests with a home away from home! We feel our cottage offers that and much more.

Top guest favorite

The entrance to the Hillside Cottage features a wooden deck with a set of stairs leading down to the spacious lawn. The exterior combines natural stone with warm wooden panels, surrounded by lush greenery and tall trees, providing a tranquil setting.

Cottage in Whitehall

4.99 out of 5 average rating, 207 reviews

Hillside Cottage @ The Mettawee Retreat

The Hillside Cottage is a luxury cabin with views of the Mettawee River. Located on 26 acres on a back road, it is peaceful & private. Enjoy fishing, swimming, kayaking or relax on the deck. This riverside retreat includes a king bed, jacuzzi tub & a kitchenette. Sitting around the fire pit with dinner cooked on the grill is the perfect ending to a long hike. Whether it’s a quick get-away or an extended vacation, the Hillside Cottage is a simple solution from a complicated life.

Top guest favorite

A stone fireplace is seen with warm flames flickering from burning logs. The fire creates a cozy ambiance against the rustic stone backdrop, while the wooden floor reflects the light from the fire, enhancing the inviting atmosphere of the space.

Cottage in Windsor

4.97 out of 5 average rating, 393 reviews

Ogden's Mill Farm

Private guest house situated on over 250 acres, with fully equipped gourmet kitchen and great views of quiet fields and valley. Pond with diving board for swimming in the summer. Giant sledding hill is a favorite of children and adults alike. Trails on property for hiking, xc- skiing, and snowshoeing. 15 mins to Woodstock VT. 45 mins to Killington,Pico and Okemo. Great restaurants and shopping nearby. Hanover and Norwich VT 20 mins. Please note not handicapped accesible.

Guest favorite

A small deck is featured, furnished with two high-top chairs and a square table. The serene lake view is framed by tall trees, and the sky is filled with scattered clouds. The deck is situated above grassy areas, enhancing the tranquil setting.

Cottage in Castleton

4.87 out of 5 average rating, 130 reviews

Family or couples retreat on Lake Bomoseen

Newly Renovated! Now 3 bedrooms 2 baths and relax and take in the lake views in the new decks. Great for a small family or couples retreat. Boat slip and dock and 100 feet of frontage for your use on the lake. Fully stocked kitchen. Just Bring your SHEETS and TOWELS. Sunsets are great! Lake activities or hiking, biking. We are year round! 20 Mins from Rutland, 30 Mins. from Skiing! Please bring your own boat or kayak otherwise rent No large parties or events

Guest favorite

A printed notice is displayed, emphasizing the importance of reading house rules prior to booking. The text is centered within a black border, providing clear visibility against the light background.

Cottage in Moriah

4.99 out of 5 average rating, 157 reviews

Pearl of the Mountain

The Beebe Farm was started in 1921 by Fred and Pearl Beebe. There are now four generations of Beebe's who have farmed this land. Over time these spectacular views have been created by hard work and devotion to agriculture. We offer this rental for you to relax and enjoy the breathtaking panorama of Lake Champlain, the Green Mountains of Vermont, and the eastern slopes of the Adirondacks. Many activities and attractions can be found close by!

Guest favorite

A serene winter scene is captured, featuring a snow-covered pathway leading through a landscape of white. Historic buildings, including a red structure and a stone wall, are visible amid trees blanketed in snow, set against a backdrop of a clear blue sky.

Cottage in Pawlet

4.92 out of 5 average rating, 190 reviews

The Smithy Cottage at Consider Bardwell Farm

The historic “Smithy" at Consider Bardwell Farm is the original building used for blacksmithing by Consider Bardwell, himself, in the 1800s. Complete with brand-new, architect-designed kitchen and bathroom, wood-burning fireplace, and stone patio for outdoor grilling and dining, the Smithy is beautiful inside and out. Enjoy meeting our goats and all the local goodies and products that we can stock in your cottage.

Top guest favorite

Three sheep graze in an open field, surrounded by autumn foliage displaying vibrant hues of red, orange, and green. The background features rolling hills that extend towards the horizon, reflecting the beauty of the changing seasons.

Cottage in Hartland

4.97 out of 5 average rating, 457 reviews

Breeze Hill Cottage

This cozy two bedroom cottage sits on a well-maintained dirt road overlooking fields, woods, and the NH mountains. Watch birds from the window, relax on the patio, and enjoy the flower gardens. The cottage boasts modern amenities mixed with antiques. Please note: if we don’t respond to an Airbnb message and you need to speak with us, call us!